European Journal of Organic Chemistry

Cover image for Vol. 2016 Issue 21

Early View (Online Version of Record published before inclusion in an issue)

Editor: Haymo Ross, Deputy Editor: Anne Nijs

Impact Factor: 3.068

ISI Journal Citation Reports © Ranking: 2015: 17/59 (Chemistry Organic)

Online ISSN: 1099-0690

Associated Title(s): Advanced Synthesis & Catalysis, Asian Journal of Organic Chemistry

VIEW

  1. 1 - 60
  1. Microreviews

    1. Catalyzed Stereoselective Glycosylation

      Glycosylation via Transition-Metal Catalysis: Challenges and Opportunities

      Xiaohua Li and Jianglong Zhu

      Version of Record online: 21 JUL 2016 | DOI: 10.1002/ejoc.201600484

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      Development of efficient, mild, and easily operable stereoselective glycosylations is of critical importance to access sufficient amounts of pure and structurally well-defined carbohydrates for studies of their biological functions. Such studies will facilitate our understanding of the role of complex oligosaccharides and glycoconjugates in biological processes as well as the development of carbohydrate-based effective therapeutic agents. This review highlights recent advances in the transition metal catalyzed stereoselective glycosylations for the synthesis of a variety of structurally complex and biologically significant O-, N-, C-, and S-glycosides.

    2. Copper Catalysis

      Emergence of Copper-Mediated Formation of C–C Bonds

      Carine Maaliki, Emilie Thiery and Jérôme Thibonnet

      Version of Record online: 21 JUL 2016 | DOI: 10.1002/ejoc.201600540

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      An overview of copper-catalyzed C–C bond reactions through the main recently developed methodologies is presented.

    3. Dimeric Pyranonaphthoquinones

      Dimeric Pyranonaphthoquinones: Isolation, Bioactivity, and Synthetic Approaches

      Rodney A. Fernandes, Pradnya H. Patil and Dipali A. Chaudhari

      Version of Record online: 21 JUL 2016 | DOI: 10.1002/ejoc.201600544

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      The dimeric pyranonaphthoquinones, “bis versions” of the naphtho[2,3-c]pyran-5,10-dione moiety, comprises a group of antibiotics that have been isolated from a variety of sources including plants, bacteria, fungi, and insects. This review discusses the naturally occurring dimeric pyranonaphthoquinones, their isolation and bioactivity, and synthetic approaches toward them.

  2. Full Papers

    1. Organic Photovoltaics

      Synthesis and Characterization of Squaraine-Based Photocrosslinkable Resists for Bulk Heterojunction Solar Cells

      Riccardo Turrisi, Luca Mascheroni, Mauro Sassi, Myles Rooney, Nunzio Buccheri, Riccardo Ruffo, Antonio Facchetti and Luca Beverina

      Version of Record online: 21 JUL 2016 | DOI: 10.1002/ejoc.201600552

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      The use of functional photoresists based on acrylic functionalized squaraines enables the preparation of solvent resistant small molecule-based Organic Bulk Heterojunction solar cells. The photocrosslinking process improves conversion efficiencies with respect to the corresponding unexposed devices.

    2. Isoxazolidine Synthesis

      Construction of Isoxazolidines through Formal [3+2] Cycloaddition Reactions of in situ Generated Nitrosocarbonyls with Donor–Acceptor Cyclopropanes: Synthesis of α-Amino γ-Butyrolactones

      Rohit Kumar Varshnaya and Prabal Banerjee

      Version of Record online: 21 JUL 2016 | DOI: 10.1002/ejoc.201600582

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      MgI2-catalyzed [3+2] cycloaddition reactions of donor–acceptor cyclopropanes with in situ generated nitrosocarbonyls from hydroxycarbamates is explored for the synthesis of functionalized isoxazolidines. Furthermore, isoxazolidines readily transformed into synthetically important α-amino-γ-butyrolactones.

    3. tert-Butylating Reagent

      Development of a Triazine-Based tert-Butylating Reagent, TriAT-tBu

      Kohei Yamada, Naoko Hayakawa, Hikaru Fujita, Masanori Kitamura and Munetaka Kunishima

      Version of Record online: 21 JUL 2016 | DOI: 10.1002/ejoc.201600663

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      A new tert-butylating reagent, 2,4,6-tris(tert-butoxy)-1,3,5-triazine (TriAT-tBu) has been developed for the acid-catalyzed tert-butylation of alcohols and carboxylic acids. The reaction of various alcohols and carboxylic acid with TriAT-tBu in the presence of a catalytic amount of an acid provided the corresponding tert-butyl ethers and esters in good yields.

    4. Benzofuroxans

      A Synthetic Pathway to Substituted Benzofuroxans through the Intermediacy of Sulfonates: The Case Example of Fluoro-Nitrobenzofuroxans

      Cyril Jovené, Jérome Marrot, Jean-Philippe Jasmin, Elena Chugunova and Régis Goumont

      Version of Record online: 21 JUL 2016 | DOI: 10.1002/ejoc.201600657

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      4-Fluoro-6-nitrobenzofuroxan and 6-fluoro-4-nitrobenzofuroxan have been prepared, for the first time, from fluorophenols and fluoroanisoles, two families of cheap and readily available chemicals. Due to the presence of methoxy and hydroxy groups, the key nitration step is easily achieved and dinitro compounds are obtained in good yields; these can then be used to prepare the phenyl azide intermediate.

    5. Cyclopropa[b]chromanones

      Catalytic One-Pot Diastereoselective Michael-Initiated Ring-Closure of Methyl Ketones with 3-Bromochromones: Synthesis of Cyclopropa[b]chromanones

      Joana L. C. Sousa, Oualid Talhi, Ricardo F. Mendes, Filipe A. Almeida Paz, Khaldoun Bachari and Artur M. S. Silva

      Version of Record online: 21 JUL 2016 | DOI: 10.1002/ejoc.201600413

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      A one-pot diastereoselective base-catalyzed Michael-initiated ring closure (MIRC) of activated methyl ketones with 3-bromochromones to give cyclopropa[b]chromanones is described. 1-Acetyl-substituted cyclopropa[b]chromanones undergo a consecutive MIRC reaction with a second molecule of 3-bromochromone to give the first described 1,1′-carbonylbis(cyclopropa[b]chromanone) dimers as a meso form.

    6. Methacrylate Natural Products

      Cyaneodimycin, a Bioactive Compound Isolated from the Culture of Streptomyces cyaneofuscatus Associated with Lichina confinis

      Delphine Parrot, Nathalie Legrave, Laurent Intertaglia, Isabelle Rouaud, Patrick Legembre, Martin Grube, Marcelino T. Suzuki and Sophie Tomasi

      Version of Record online: 21 JUL 2016 | DOI: 10.1002/ejoc.201600252

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      Two new methacrylate derivatives [cyaneodimycin (1) and cyaneomycin (2)] were isolated from the culture of Streptomyces cyaneofuscatus (MOLA1488) associated with Lichina confinis along with 6 other known compounds. Notably, compound 1 was shown to display low cytotoxicity against B16, HaCaT and Jurkat cells lines.

    7. Luminescence

      Highly Luminescence Anthracene Derivatives as Promising Materials for OLED Applications

      Aneta Slodek, Michal Filapek, Ewa Schab-Balcerzak, Marzena Grucela, Sonia Kotowicz, Henryk Janeczek, Karolina Smolarek, Sebastian Mackowski, Jan Grzegorz Malecki, Agnieszka Jedrzejowska, Grazyna Szafraniec-Gorol, Anna Chrobok, Beata Marcol, Stanislaw Krompiec and Marek Matussek

      Version of Record online: 19 JUL 2016 | DOI: 10.1002/ejoc.201600532

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      Symmetrical anthracene derivatives with bulky units connected to the anthracene frame through an ethynyl bridge were synthesized and their electrochemical, photophysical, and electrical properties were characterized. The compounds were yellowish-orange emitters with high thermal stability, had excellent solubility in most organic solvents, and very high photoluminescence quantum yield in solution.

    8. Asymmetric Catalysis

      Enantioselective Cascade Reaction of α-Cyano Ketones and Isatylidene Malononitriles: Asymmetric Construction of Spiro[4H-pyran-oxindoles]

      Jin Xie, Wei-Long Xing, Feng Sha and Xin-Yan Wu

      Version of Record online: 19 JUL 2016 | DOI: 10.1002/ejoc.201600432

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      α-Cyano ketones have been used for the first time as Michael donors in the construction of chiral spiro compounds. In the presence of only 2 mol-% of a chiral multifunctional organocatalyst, chiral spiro[4H-pyran-oxindole] derivatives were prepared in excellent yields with good-to-excellent enantioselectivities. This method provides a new approach to the synthesis of chiral spirocyclic oxindoles.

    9. C–H Activation

      Ruthenium-Catalyzed C–H Amidation and Alkenylation of Cyclic N-Sulfonyl Ketimines

      Ramasamy Manoharan and Masilamani Jeganmohan

      Version of Record online: 19 JUL 2016 | DOI: 10.1002/ejoc.201600505

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      Cyclic N-sulfonyl ketimines undergo highly regioselective ruthenium-catalyzed C–H amidation or alkenylation reactions with organic sulfonyl azides or alkenes.

    10. Synthesis of Carbocycles

      Synthesis of 1,2,3,4,5,6,7-Heptasubstituted Cycloheptatrienes through Cycloaddition Reactions of Substituted Cyclopentadienones

      Dmitry N. Platonov, Aleksandr Yu. Belyy, Ivan V. Ananyev and Yury V. Tomilov

      Version of Record online: 19 JUL 2016 | DOI: 10.1002/ejoc.201600516

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      Regioselective convergent three- to four-step synthesis of heptasubstituted cycloheptatrienes with a wide range of substituents on the cycle was carried out, starting from 2-oxo-4,5-diphenylcyclopenta-3,5-diene-1,3-dicarboxylate and 2,3-dimethyl(2,3-diphenyl)cycloprop-2-ene-1-carboxylates or 2-diazo-3-(trifluoromethyl)butenoates.

    11. Multicomponent Reactions

      Indoline-Based Constrained Peptidomimetic Motifs Obtained via the Joullié–Ugi Reaction of Indolenines

      Pavel Golubev, Olga Bakulina, Dmitry Dar'in and Mikhail Krasavin

      Version of Record online: 19 JUL 2016 | DOI: 10.1002/ejoc.201600656

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      The scope of the Joullié–Ugi reaction was extended to sterically demanding (and often unstable to isolation) indolenines. This has resulted in a new type of conformationally constrained peptidomimetic compounds.

  3. Communications

    1. Asymmetric Synthesis

      Consecutive Pictet–Spengler Condensations toward Bioactive 8-Benzylprotoberberines: Highly Selective Total Syntheses of (+)-Javaberine A, (+)-Javaberine B, and (–)-Latifolian A

      Jenifer Kayhan, Martin J. Wanner, Steen Ingemann, Jan H. van Maarseveen and Henk Hiemstra

      Version of Record online: 19 JUL 2016 | DOI: 10.1002/ejoc.201600764

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      Double Pictet–Spengler (PS) methodology for triple selectivity: Three indole alkaloids were synthesized by first using a chiral Brønsted acid catalyzed enantioselective PS condensation, followed by a second diastereoselective PS reaction, of which the regioselectivity was controlled through the right choice of the reaction solvent.

  4. Full Papers

    1. Carbohydrate Sulfonic Acids

      Synthesis of C-2- and C-3-Sulfonatomethyl O- and S-Glycosides by Horner–Wadsworth–Emmons Olefination

      Dániel Eszenyi, Attila Mándi, Mihály Herczeg, Attila Bényei, István Komáromi and Anikó Borbás

      Version of Record online: 18 JUL 2016 | DOI: 10.1002/ejoc.201600526

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      The Horner–Wadsworth–Emmons olefination has been applied to the synthesis of thioglycosides bearing a secondary sulfonatomethyl moiety as potential building blocks for the synthesis of biorelevant sulfated oligosaccharides. The configurations and conformations of the products were investigated by NMR spectroscopy, X-ray diffraction, and molecular dynamics.

    2. Natural Product Synthesis

      A Total Synthesis of (–)-Nardoaristolone B

      Rohini S. Ople, Kishor L. Handore, Nidhi S. Kamat and D. Srinivasa Reddy

      Version of Record online: 18 JUL 2016 | DOI: 10.1002/ejoc.201600538

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      A stereoselective total synthesis of (–)-Nardoaristolone B, a nor-aristolane sesquiterpenoid natural product with an unusual 3/5/6 tricyclic ring system is described. Use of (+)-(R)-Pulegone as a chiral-pool starting material, ring closing metathesis and stereoselective cyclopropanation are the highlights.

    3. Anion Binding

      Synthesis and Multi-Oxo Anion-Binding Properties of Oligopyrrolic Macrocycles Based on Naphthobipyrrole

      Abeje Abebayehu, Ranjan Dutta, Soo-Jin Kim, Ji Hye Lee, Hyonseok Hwang and Chang-Hee Lee

      Version of Record online: 18 JUL 2016 | DOI: 10.1002/ejoc.201600547

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      A new class of oligopyrrolic macrocycles containing naphthobipyrrole units displays strong and selective binding affinity towards dihydrogen phosphate anions.

    4. Bent Transition States

      Effects of Angular Deformation on the Energetics of the SN2 Reaction

      Vincent de Paul N. Nziko and Steve Scheiner

      Version of Record online: 18 JUL 2016 | DOI: 10.1002/ejoc.201600712

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      The classic SN2 reaction is thought to progress through a linear transition state, but nonlinearity can be imposed by enzymes. Quantum calculations show that such imposed distortion has little effect upon the activation energy. This lack of sensitivity arises, because the energy of the transition state is raised by the distortion, but so is that of the reaction complex.

    5. Dicarboxylate Anion Binding

      Preorganized Fluorescent Receptor for the Preferential Binding of the Glutarate Anion

      Miriam Más-Montoya, David Curiel, Carmen Ramírez de Arellano, Alberto Tárraga and Pedro Molina

      Version of Record online: 18 JUL 2016 | DOI: 10.1002/ejoc.201600521

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      A carbazolo[1,2-a]carbazole-2,11-dicarboxamide was employed as a dianion receptor that affords a size-selective response when a homologous series of dicarboxylates are analyzed. Interestingly, a preferential ratiometric fluorescent response was observed for the glutarate anion during the recognition process, which produced an evident color change in the emitted light.

    6. Amino Acid Synthesis

      Synthesis of α-Propargylglycinates Using the Borono-Mannich Reaction with Pinacol Allenylboronate and Potassium Allenyltrifluoroborate

      Rachel K. Chambers, Nattapong Chaipukdee, Thanaphat Thaima, Kwanjai Kanokmedhakul and Stephen G. Pyne

      Version of Record online: 14 JUL 2016 | DOI: 10.1002/ejoc.201600436

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      A regioselective synthesis of α-propargylglycinates using the borono-Mannich reaction has been developed.

    7. Difluoromethylation

      AgI-Promoted Cascade for Difluoromethylation of Activated Alkenes to Difluoromethylated Oxindoles

      Xinglu Wang, Wen Wan, Yunrong Chen, Jialiang Li, Haizhen Jiang, Yong Wang, Hongmei Deng and Jian Hao

      Version of Record online: 14 JUL 2016 | DOI: 10.1002/ejoc.201600461

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      A highly efficient synthesis of various difluoro-containing oxindoles has been achieved by using the described AgI-mediated direct difluoromethylation reaction of activated alkenes.

    8. Michael Addition

      Synthesis of (+)-Antroquinonol and Analogues by Using Enantioselective Michael Reactions of Benzoquinone Monoketals

      Che-Sheng Hsu and Jim-Min Fang

      Version of Record online: 14 JUL 2016 | DOI: 10.1002/ejoc.201600542

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      The electron-withdrawing chloro group has been employed as a surrogate of a methoxy substituent to facilitate the enantioselective Michael reaction, which is the key strategic step in the short and efficient synthesis of (+)-antroquinonol.

    9. Hydroquinone Synthesis

      Biomass-Based and Oxidant-Free Preparation of Hydroquinone from Quinic Acid

      Benedicta Assoah, Luis F. Veiros, Carlos A. M. Afonso and Nuno R. Candeias

      Version of Record online: 14 JUL 2016 | DOI: 10.1002/ejoc.201600616

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      Hydroquinone from a non-fossil source: Hydroquinone has been prepared from a biomass-based starting material by a metal- and oxidant-free process. Polymer-based Amberlyst-15 in the dry form promoted the conversion of quinic acid into hydroquinone under mild conditions, whereas uncatalysed processes demanded unpractical reaction conditions.

    10. Tandem Reactions

      N,2,3,4-Tetrasubstituted Pyrrolidines through Tandem Lithium Amide Conjugate Addition/Radical Cyclization/Oxygenation Reactions

      František Kafka, Radek Pohl, Ivana Císařová, Richard Mackman, Gina Bahador and Ullrich Jahn

      Version of Record online: 14 JUL 2016 | DOI: 10.1002/ejoc.201600621

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      Readily available chiral allylic amines and α,β-unsaturated esters are used to synthesize densely substituted pyrrolidines with exclusive 2,3-trans and up to 6:1 3,4-cis/trans configuration in a tandem polar lithium amide conjugate addition/radical cyclization/oxygenation sequence.

  5. Communications

    1. Meta Alkylation

      A Mild meta-Selective C–H Alkylation of Catechol Mono-Ethers

      Edon Vitaku and Jon T. Njardarson

      Version of Record online: 14 JUL 2016 | DOI: 10.1002/ejoc.201600760

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      Catechol mono-ethers are dearomatized via lead(IV) acetate then reacted with trialkylboranes to give net meta-alkylated products. Primary, secondary and tertiary radicals can be added, and the method is compatible with reactive groups on the parent arene.

  6. Full Papers

    1. Macrocyclic Phostones

      Synthesis of Benzothiophene-Containing 10- and 11-Membered Cyclic Phostones

      Alexios N. Matralis and Youla S. Tsantrizos

      Version of Record online: 13 JUL 2016 | DOI: 10.1002/ejoc.201600333

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      Phostones are useful transition-state analogues of proteases and substrate mimics of DNA/RNA-processing enzymes. Methodologies for the preparation of medium-sized ring phostones are developed that are amenable to the parallel synthesis of structurally diverse derivatives containing a benzo[b]thiophene core, which thus enables profiling of such molecules in biological screens.

  7. Microreviews

    1. Organocatalysis

      Enantioselective Catalysis by Chiral Isothioureas

      Jérémy Merad, Jean-Marc Pons, Olivier Chuzel and Cyril Bressy

      Version of Record online: 13 JUL 2016 | DOI: 10.1002/ejoc.201600399

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      Molecular Swiss Army Knives! This review covers the reactivity of chiral isothioureas, which emerged as nucleophilic organocatalysts in 2006. Multiple modes of activation rapidly came to be displayed by these heterocycles; this now makes them powerful catalysts in the toolbox of the organic chemist.

  8. Communications

    1. C–H Activation

      Amino Acid Ligands for Ruthenium(II)-Catalyzed C–H Arylation of Aryltetrazoles with Chlorides: Expedient Access to Antihypertension Drugs

      Jonathan Hubrich and Lutz Ackermann

      Version of Record online: 13 JUL 2016 | DOI: 10.1002/ejoc.201600742

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      Ruthenium(II) complexes derived from amino acids enable the first general C–H arylations of aryltetrazoles with inexpensive aryl chlorides. The user-friendly Piv-Val-OH-based ruthenium(II) catalyst has broad substrate scope, excellent functional group tolerance, and high catalytic activity. Thereby, the ruthenium(II) catalysis allows the step-economical preparation of the antihypertension drug Valsartan.

    2. Domino Reactions

      Copper(II) Trifluoromethanesulfonate Catalyzed Hydroamination Cyclization–Dimerization Cascade Reaction of Homopropargylic Amines for the Construction of Complex Fused Nitrogen-Containing Tetracycles

      Lingyan Liu, Chan Wang, Qiangqiang Liu, Yuanfang Kong, Weixing Chang and Jing Li

      Version of Record online: 13 JUL 2016 | DOI: 10.1002/ejoc.201600692

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      A Cu(OTf)2-catalyzed intramolecular radical hydroamination cyclization–dimerization cascade reaction of simple homopropargylic amines is developed, and a complex nitrogen-containing tetracyclic framework is constructed in one pot with the formation of four new bonds and five stereocenters. Noteworthy, the aglycon of the natural product incargranine B is facilely and efficiently synthesized.

  9. Full Papers

    1. Nitrogen Heterocycles

      NaNO2/I2-Mediated Regioselective Synthesis of Nitrosoimidazoheterocycles from Acetophenones by a Domino Process[‡]

      Sushobhan Mukhopadhyay, Shashikant U. Dighe, Shivalinga Kolle, Praveen K. Shukla and Sanjay Batra

      Version of Record online: 13 JUL 2016 | DOI: 10.1002/ejoc.201600553

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      A domino reaction between 2-aminopyridines and acetophenones in the presence of NaNO2 and I2 enables direct and efficient synthesis of nitrosoimidazoheterocycles.

    2. Alkene Metathesis

      Ring-Rearrangement-Metathesis Approach to Polycycles: Substrate-Controlled Stereochemical Outcome During Grignard Addition

      Sambasivarao Kotha and Ongolu Ravikumar

      Version of Record online: 13 JUL 2016 | DOI: 10.1002/ejoc.201600596

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      We have observed substrate-controlled selectivity in Grignard reactions of norbornene derivatives to generate either syn- or anti-addition products. The stereochemistry of the Grignard addition products was confirmed by single-crystal X-ray diffraction studies. Highly decorated norbornene derivatives were subjected to ring-rearrangement metathesis to deliver intricate polycycles.

    3. Cross-Linking in OLEDs

      Thermally Cross-Linkable Host Materials for Solution-Processed OLEDs: Synthesis, Characterization, and Optoelectronic Properties

      Yuanju Tang, Jinyong Zhuang, Liming Xie, Xiaolian Chen, Dongyu Zhang, Jian Hao, Wenming Su and Zheng Cui

      Version of Record online: 12 JUL 2016 | DOI: 10.1002/ejoc.201600407

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      A series of cross-linkable bipolar host materials containing carbazole donor and 1,2,4-triazole acceptor were designed and synthesized. The host materials with styryl groups can be thermally cross-linked without any polymerization initiator, and all showed excellent solvent resistance. The calculated HOMOs indicate low injection barrier from the hole transport layer. A current efficiency of 15.3 cd A–1 and EQE of 4.6 % were achieved for solution-processed Ir(mppy)3-based OLEDs.

    4. C–H Acylation

      Regioselective ortho-Acylation of N-Aryl-1,2,3-triazoles with Alcohols in Water

      Chanchal Premi, Shyam Sunder Patel and Nidhi Jain

      Version of Record online: 12 JUL 2016 | DOI: 10.1002/ejoc.201600479

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      A palladium-catalyzed regioselective ortho-acylation of N-aryl-1,2,3-triazoles with benzylic, heterocyclic, and aliphatic alcohols has been achieved under aqueous conditions to give the corresponding triazole-substituted ketones in moderate to high yields. TBHP = tert-butyl hydroperoxide.

    5. Reduction

      Serendipitous Synthesis of (tert-Butyl-NNO-azoxy)acetonitrile: Reduction of an Oxime Moiety to a Methylene Unit

      Michael S. Klenov, Oleg V. Anikin, Alexey A. Guskov, Aleksandr M. Churakov, Yurii A. Strelenko, Ivan V. Ananyev, Ivan S. Bushmarinov, Artem O. Dmitrienko, Konstantin A. Lyssenko and Vladimir A. Tartakovsky

      Version of Record online: 12 JUL 2016 | DOI: 10.1002/ejoc.201600584

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      (tert-Butyl-NNO-azoxy)acetonitrile was obtained by a new one-step transformation of an oxime group into a methylene unit using an aminating agent. This active-methylene compound has played a key role in creating a new approach to the synthesis of tetrazole 1-oxides.

    6. Multivalent Calix[4]arenes

      An Efficient Multi-Component Synthesis of Highly Functionalized Calix[4]arenes with Pronounced Binding Affinity toward β-Lactoglobulin

      Reza Zadmard, Peyman Akbari-Moghaddam, Shukufe Darvishi and Maryam Mirza-Aghayan

      Version of Record online: 11 JUL 2016 | DOI: 10.1002/ejoc.201600543

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      A new class of highly functionalized calix[4]arenes was synthesized by multi-component reactions in good yields (70–86 %). Protein-binding studies carried out with fluorescence spectroscopy revealed that these compounds bind strongly to β-lactoglobulin.

  10. Communications

    1. Transesterification

      Chemoselective Transesterification of Acrylate Derivatives for Functionalized Monomer Synthesis Using a Hard Zinc Alkoxide Generation Strategy

      Daiki Nakatake, Ryo Yazaki and Takashi Ohshima

      Version of Record online: 11 JUL 2016 | DOI: 10.1002/ejoc.201600737

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      We develop a highly chemoselective transesterification of acrylate derivatives by using a hard zinc alkoxide generation strategy. High functional group compatibility, including the hydrophilic ether functionality, clearly demonstrates the utility of the present zinc catalysis for the synthesis of functionalized monomers.

  11. Full Papers

    1. FRET Rods

      FRET Pairs with Fixed Relative Orientation of Chromophores

      Pablo Wessig, Nicole Behrends, Michael U. Kumke and Ursula Eisold

      Version of Record online: 11 JUL 2016 | DOI: 10.1002/ejoc.201600489

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      FRET pairs with a fixed relative orientation of chromophores have been synthesized by combining fluorophores with oligospirothioketal (OSTK) rods. Their photophysical properties have been investigated and are described herein.

    2. Iron Catalysis

      Iron-Catalyzed Synthesis of Five-Membered Cyclic Carbonates from Vicinal Diols: Urea as Sustainable Carbonylation Agent

      Miguel Peña-López, Helfried Neumann and Matthias Beller

      Version of Record online: 8 JUL 2016 | DOI: 10.1002/ejoc.201600476

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      A new catalytic approach for the synthesis of five-membered cyclic carbonates from the reaction of urea with vicinal diols has been developed. The use of an inexpensive nontoxic iron catalyst and readily available substrates in combination with the resulting high atom economy make this an operationally simple and sustainable process.

  12. Communications

    1. Bis-Phosphorus Complex

      A Mixed-Valence Bis-Phosphorus Complex Entrapped in a Oxatriphyrin(3.1.1) Surrounding

      Aneta Idec, Janusz Skonieczny, Lechosław Latos-Grażyński and Miłosz Pawlicki

      Version of Record online: 8 JUL 2016 | DOI: 10.1002/ejoc.201600701

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      Oxatriphyrin(3.1.1) forms a rare, mixed-valence bis-phosphorus complex of unprecedented orientation. The flexibility of the macrocycle allows the incorporation of a PIII–O–PV unit. Oxidation gives a product in which two phosphorus ions compete for a bridging oxygen atom, which results in the liberation of POCl and quantitative conversion into a monophosphorus complex.

  13. Full Papers

    1. Organocatalysts

      Simple Primary Amino Amide Organocatalyst for Enantioselective Aldol Reactions of Isatins with Ketones

      Jo Kimura, Ummareddy Venkata Subba Reddy, Yoshihito Kohari, Chigusa Seki, Yasuteru Mawatari, Koji Uwai, Yuko Okuyama, Eunsang Kwon, Michio Tokiwa, Mitsuhiro Takeshita, Tatsuo Iwasa and Hiroto Nakano

      Version of Record online: 8 JUL 2016 | DOI: 10.1002/ejoc.201600414

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      New simple primary amino amide organocatalysts display a high degree of activity in asymmetric aldol reactions between isatins and alkanones to afford optically active 3-hydroxy-2-oxindoles.

    2. Selective N-Alkylation

      Cs2CO3-Promoted Direct N-Alkylation: Highly Chemoselective Synthesis of N-Alkylated Benzylamines and Anilines

      Juan-Carlos Castillo, Jessica Orrego-Hernández and Jaime Portilla

      Version of Record online: 8 JUL 2016 | DOI: 10.1002/ejoc.201600549

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      This paper describes the development of a highly chemoselective methodology for the direct mono-N-alkylation of primary aliphatic and aromatic amines with a broad range of alkyl halides. Cesium carbonate serves as the base and no additive or catalyst is required thus underscoring the crucial role of the “cesium effect” on the formation of secondary amines as the major products.

    3. Amide Allylation

      Nickel(0)-Catalyzed N-Allylation of Amides and p-Toluenesulfonamide with Allylic Alcohols under Neat and Neutral Conditions

      Mohamed Salah Azizi, Youssef Edder, Abdallah Karim and Mathieu Sauthier

      Version of Record online: 8 JUL 2016 | DOI: 10.1002/ejoc.201600500

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      Amides and p-toluenesulfonamide are N-allylated using allyl alcohol in a catalytic fashion. The reaction is promoted by nickel-based catalysts and yields water as a byproduct. Interestingly, self-etherification of allylic alcohol is a competing side reaction that yields diallyl ether.

    4. Gold Catalysis

      Gold-Catalyzed Cycloisomerization of Alkyne-Containing Amino Acids: Controlled Tuning of C–N vs. C–O Reactivity

      Noelia S. Medran, Matías Villalba, Ernesto G. Mata and Sebastián A. Testero

      Version of Record online: 6 JUL 2016 | DOI: 10.1002/ejoc.201600429

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      A gold-catalyzed C–N and C–O functionalization of alkyne-containing amino acids is described. The strategy disclosed here enables the divergent synthesis of alkylidenelactones and 1-pyrrolines derived from amino acids.

    5. Natural Product Synthesis

      Late-Stage Bromination Enables the Synthesis of Rubrolides B, I, K, and O

      Milandip Karak, Jaime A. M. Acosta, Luiz C. A. Barbosa and John Boukouvalas

      Version of Record online: 6 JUL 2016 | DOI: 10.1002/ejoc.201600473

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      The first total synthesis of the marine natural metabolites rubrolides B, I, K and O is described; this approach employs a site-selective Suzuki coupling, vinylogous aldol condensation and a late-stage regioselective bromination.

    6. Spin Switching

      Spin State Switching in Solution with an Azoimidazole-Functionalized Nickel(II)-Porphyrin

      Gernot Heitmann, Christian Schütt and Rainer Herges

      Version of Record online: 6 JUL 2016 | DOI: 10.1002/ejoc.201600548

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      Spin switching in solution at ambient temperature is reported for an azoimidazole-functionalized Ni2+-porphyrin. Upon irradiation with either UV or blue light, N-methylimidazole reversibly coordinates to the Ni2+ ion. Consequently, Ni2+ undergoes light-driven coordination-induced spin state switching between a diamagnetic (S = 0) and a paramagnetic (S = 1) spin state.

    7. Radical Reactions

      Catalyst-Free S–S Bond Insertion Reaction of a Donor/Acceptor-Free Carbene by a Radical Process: A Combined Experimental and Computational Study

      Yang Zheng, Rongjian Bian, Xiaolu Zhang, Ruwei Yao, Lihua Qiu, Xiaoguang Bao and Xinfang Xu

      Version of Record online: 6 JUL 2016 | DOI: 10.1002/ejoc.201600664

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      A donor/acceptor-free carbene insertion reaction of an S–S bond through a radical process is presented. This catalyst-free reaction was thermally induced and provided the dithioketal products in moderate to high yields. A mechanism involving radical intermediates was proposed according to the computational study, and these intermediates were identified in a cross-coupling reaction.

  14. Microreviews

    1. Manganese Catalysis

      Recent Advances of Manganese Catalysis for Organic Synthesis

      Jonathan R. Carney, Barry. R. Dillon and Stephen P. Thomas

      Version of Record online: 4 JUL 2016 | DOI: 10.1002/ejoc.201600018

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      The manganese-catalysed functionalisation of organic molecules is reviewed with regard to synthetic applications. Manganese-catalysed C–H oxidations, halogenations, cross-couplings and C–H activations are discussed with mechanisms details.

    2. Asymmetric Catalysis

      Shibasaki Catalysts and Their Use for Asymmetric Synthetic Applications by the Chemical Industry

      Harald Gröger

      Version of Record online: 4 JUL 2016 | DOI: 10.1002/ejoc.201600174

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      Shibasaki catalysts are a unique, highly efficient, and broadly applicable class of catalysts for use in asymmetric synthesis. It is these catalytic properties that make them attractive for industrial applications, and companies such as Actelion Pharmaceuticals, Nissan Chemicals, Hokko Chemicals, SKW Trostberg, and Sumitomo Dainippon Pharma jointly with Sunovion Pharmaceuticals have been involved in activities for their commercial use.

    3. Enzyme Catalysis

      Thiamine-Diphosphate-Dependent Enzymes as Catalytic Tools for the Asymmetric Benzoin-Type Reaction

      Pier Paolo Giovannini, Olga Bortolini and Alessandro Massi

      Version of Record online: 27 JUN 2016 | DOI: 10.1002/ejoc.201600228

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      Thiamine-diphosphate-dependent (ThDP-dependent) enzymes are very efficient catalysts for asymmetric benzoin-type condensation. Through chemo- and stereoselective coupling of various carbonyl reagents promoted by enzymes of this family a wide variety of optically active α-hydroxy ketones have been produced. An overview of these synthetically relevant enzymatic benzoin-type reactions is given.

    4. Dynamic Systems

      The Dynamic Covalent Chemistry of Esters, Acetals and Orthoesters

      René-Chris Brachvogel and Max von Delius

      Version of Record online: 27 JUN 2016 | DOI: 10.1002/ejoc.201600388

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      This microreview discusses the fundamental aspects of three related reversible covalent reactions and their uses in dynamic combinatorial libraries and the self-assembly of stimuli-responsive molecules and materials.

    5. Cross Dehydrogenative Coupling

      Cross Dehydrogenative Coupling (CDC) Reactions of N,N-Disubstituted Formamides, Benzaldehydes and Cycloalkanes

      Aanchal Batra, Paramjit Singh and Kamal Nain Singh

      Version of Record online: 27 JUN 2016 | DOI: 10.1002/ejoc.201600401

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      Cross dehydrogenative coupling reactions for carbon–carbon and carbon-heteroatom bond formation have experienced significant progress with substrates such as formamides, benzaldehydes and cycloalkanes. This microreview summarizes such bond formation reactions in substrates that variously are not arylated (e.g., DMF), do not contain a heteroatom (benzaldehydes) or both (cycloalkanes).

  15. Full Papers

    1. Carbohydrate Conjugation

      You have full text access to this OnlineOpen article
      The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations

      Cornelia Hojnik, Anne Müller, Tobias-Elias Gloe, Thisbe K. Lindhorst and Tanja M. Wrodnigg

      Version of Record online: 27 JUN 2016 | DOI: 10.1002/ejoc.201600458

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      Amadori rearrangement employing (i) diamines, (ii) more complex amino-functionalized glycosides, and (iii) amino acids, as amino components for the synthesis of C-glycosyl-type neoglycoconjugates is described.

    2. Fluorinated Hexasaccharides

      Synthesis of a Fluorinated Sialophorin Hexasaccharide–Threonine Conjugate for Fmoc Solid-Phase Glycopeptide Synthesis

      Markus Daum, Frederik Broszeit and Anja Hoffmann-Röder

      Version of Record online: 27 JUN 2016 | DOI: 10.1002/ejoc.201600523

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      A first total synthesis of a fluorinated hexasaccharide–threonine antigen mimic has been accomplished using a [3+3′]-block glycosylation strategy to access novel sialophorin-derived molecular tools for biomedical and immunological studies.

  16. Microreviews

    1. Unnatural Amino Acids

      Synthesis of α-Ethynyl Glycines

      Jekaterina Bolsakova and Aigars Jirgensons

      Version of Record online: 23 JUN 2016 | DOI: 10.1002/ejoc.201600253

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      This microreview gives an overview of the methods published from 1996 to 2015 for the syntheses of ethynyl glycines and synthetically equivalent ethynyl glycinols in racemic and enantioenriched form. These derivatives can serve as versatile building blocks for the preparation of biologically active compounds, including natural products.

  17. Full Papers

    1. Natural Products

      Activation and Identification of NC-1: A Cryptic Cyclodepsipeptide from Red Soil-Derived Streptomyces sp. FXJ1.172

      Minghao Liu, Ning Liu, Fei Shang and Ying Huang

      Version of Record online: 19 JUN 2016 | DOI: 10.1002/ejoc.201600297

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      A novel cyclodepsipeptide, NC-1, was discovered from Streptomyces sp. FXJ1.172 by genome mining. It contains an entirely different amino acid composition in the core depsipeptide structure from the other cyclodepsipeptides as well as an epoxidized and longer alkyl side chain on the cinnamoyl group.

  18. Microreviews

    1. Aziridine Synthesis

      The Synthesis of Cyclophellitol-Aziridine and Its Configurational and Functional Isomers

      Jianbing Jiang, Marta Artola, Thomas J. M. Beenakker, Sybrin P. Schröder, Rita Petracca, Casper de Boer, Johannes M. F. G. Aerts, Gijsbert A. van der Marel, Jeroen D. C. Codée and Herman S. Overkleeft

      Version of Record online: 25 MAY 2016 | DOI: 10.1002/ejoc.201600472

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      Cyclophellitol-aziridine is a potent, mechanism-based and irreversible glycosidase inhibitor. It is also an excellent starting point for the development of activity-based glycosidase probes. This microreview lists the literature syntheses towards configurational and functional cyclophellitol-aziridine analogues, focusing on the two conceptual distinct strategies to introduce the aziridine moiety: by elaboration of an epimeric epoxide or by intramolecular iodo-imination from a (homo-)allylic alcohol.

    2. Anionic Cascade Reactions

      Anionic Cascade Routes to Sulfur and Nitrogen Heterocycles Originating from Thio- and Aminophosphate Precursors

      Pradipta Das and Jon T. Njardarson

      Version of Record online: 25 MAY 2016 | DOI: 10.1002/ejoc.201600312

      Thumbnail image of graphical abstract

      In this microreview article we report the synthesis of sulfur and nitrogen heterocycles via anionic cascade routes employing a phosphate group migration strategy.

  19. Full Papers

    1. Glycuronamide Synthesis

      An Oxidation–Amidation Approach for the Synthesis of Glycuronamides

      Sicheng Lin, Roger A. Ashmus and and Todd L. Lowary

      Version of Record online: 3 MAY 2016 | DOI: 10.1002/ejoc.201600239

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      A route for the synthesis of glycuronamides via the intermediacy of 6-S-tolyl-substituted glycosides and uronic acid thioesters, is reported. The route, which is compatible with a variety of carbohydrate residues and protecting groups, was used to synthesize the repeating unit of the E. coli K54 capsular polysaccharide.

  20. Microreviews

    1. Amino Alcohol Organocatalysts

      Catalytic Efficiency of Primary β-Amino Alcohols and Their Derivatives in Organocatalysis

      Ummareddy Venkata Subba Reddy, Madhu Chennapuram, Chigusa Seki, Eunsang Kwon, Yuko Okuyama and Hiroto Nakano

      Version of Record online: 26 APR 2016 | DOI: 10.1002/ejoc.201600164

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      This review demonstrates the catalytic efficiency of primary β-amino alcohols and their derivatives in organocatalysis. These simple amino alcohols are inexpensive alternatives to other primary amino organocatalysts, being easy to synthesize and air-stable and offering the potential for introduction of different functional groups and alteration of steric sites.

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